2,2-Bis(4-butyloxyphenyl)-bi-1,3,4-oxadiazole
1.86–1.80 (m, 4 H); 1.50–1.46 (m, 4 H); 1.35–1.29 (m, 24 H); 0.89
(t, 6 H, J ¼ 6.9 Hz); FT-IR (KBr disc, cmꢂ1): 2952, 2922, 2852,
1606, 1581, 1555, 1493, 1473, 1422, 1401, 1336, 1308, 1292, 1257,
1174, 1154, 1122, 1081, 1048, 1016, 996, 951, 845, 818, 741, 723,
703, 656, 632; anal. calcd for C36H50N4O4: C, 71.73; H, 8.36; N,
9.29. Found C, 71.85; H, 8.68; N, 9.35.
1H NMR: (300 MHz, CDCl3), (ppm, from TMS): 8.15 (d, 4 H, J
¼ 9.0 Hz); 7.05 (d, 4 H, J ¼ 8.9 Hz); 4.07 (t, 4 H, J ¼ 6.6 Hz);
1.82–1.78 (m, 4 H); 1.59–1.49 (m, 4 H); 1.00 (t, 6 H, J ¼ 7.2 Hz);
FT-IR (KBr disc, cmꢂ1): 2960, 2932, 2870, 1608, 1582, 1551,1493,
1470, 1424, 1336, 1308, 1288, 1272, 1256,1177, 1152, 1123,
1112,1082, 1066, 1032,1008, 1001,968, 950,910, 845, 820,
803,741, 702, 668, 653, 630; anal. calcd for C24H26N4O4: C,
66.34; H, 6.03; N, 12.89. Found C, 66.13; H, 6.12; N, 13.25.
2,2-Bis(4-cetyloxyphenyl)-bi-1,3,4-oxadiazole
1H NMR: (300 MHz, CDCl3), (ppm, from TMS): 8.16 (d, 4 H,
J ¼ 8.8 Hz); 7.05 (d, 4 H, J ¼ 8.8 Hz); 4.06 (t, 4 H, J ¼ 6.6 Hz);
1.86–1.80 (m, 4 H); 1.50–1.46 (m, 4 H); 1.35–1.26 (m, 48H); 0.88
(t, 6 H, J ¼ 6.9 Hz); FT-IR (KBr disc, cmꢂ1): 2954, 2920, 2850,
1606, 1851, 1553, 1493, 1473, 1423, 1399, 1388, 1335, 1308, 1293,
1256, 1180, 1173, 1153, 1121, 1081, 1044, 1019, 999, 974, 951,
847, 815, 740, 722, 702, 657, 632; anal. calcd for C48H74N4O4: C,
74.76; H, 9.67; N, 7.27. Found C, 74.79; H, 9.89; N, 7.40.
2,2-Bis(4-pentyloxyphenyl)-bi-1,3,4-oxadiazole
1H NMR: (300 MHz, CDCl3), (ppm, from TMS): 8.15 (d, 4 H,
J ¼ 9.0 Hz); 7.05 (d, 4 H, J ¼ 8.9 Hz); 4.06 (t, 4 H, J ¼ 6.6 Hz);
1.86–1.79 (m, 4 H); 1.50–1.40 (m, 8 H); 0.95 (t, 6 H, J ¼ 6.9 Hz);
FT-IR (KBr disc, cmꢂ1): 2948, 2921, 2870, 1608, 1582, 1493,
1476, 1462,1424, 1395, 1375,1344, 1334, 1307, 1289, 1262,1244,
1182, 1175, 1151, 1122, 1086, 1056, 1004, 951, 901, 837, 809, 741,
726, 701, 655, 630; anal. calcd for C26H30N4O4: C, 67.51; H, 6.54;
N, 12.11. Found C, 67.28; H, 6.58; N, 12.23.
Acknowledgements
The authors are grateful to the National Science Foundation
Committee of China (project no. 50373016 and 20433010),
Program for New Century Excellent Talents in Universities of
China Ministry of Education, Special Foundation for PhD
Programmes in Universities of China Ministry of Education
(Project No. 20050183057), and Project 985-Automotive
Engineering of Jilin University for their financial support of this
work.
2,2-Bis(4-hexyloxyphenyl)-bi-1,3,4-oxadiazole
1H NMR: (300 MHz, CDCl3), (ppm, from TMS): 8.15 (d, 4 H,
J ¼ 8.9 Hz); 7.04 (d, 4 H, J ¼ 8.9 Hz); 4.05 (t, 4 H, J ¼ 6.6 Hz);
1.86–1.78 (m, 4 H); 1.50–1.44 (m, 4 H); 1.38–1.35 (m, 8 H); 0.93
(t, 6 H, J ¼ 6.9 Hz); FT-IR (KBr disc, cmꢂ1): 2951, 2936, 2922,
2868, 2854, 1607, 1581, 1551, 1493, 1473, 1421, 1401, 1389, 1336,
1308, 1291, 1254, 1174, 1153, 1123, 1083, 1058, 1032, 1010, 950,
846, 819,806, 740, 702, 655, 630; anal. calcd for C28H34N4O4: C,
68.55; H, 6.99; N, 11.42. Found C, 68.31; H, 6.88; N, 11.25.
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2,2-Bis(4-heptyloxyphenyl)-bi-1,3,4-oxadiazole
1H NMR: (500 MHz, CDCl3), (ppm, from TMS): 8.17 (d, 4 H,
J ¼ 8.9 Hz); 7.06 (d, 4 H, J ¼ 8.9 Hz); 4.07 (t, 4 H, J ¼ 6.6 Hz);
1.86–1.83 (m, 4 H); 1.52–1.49 (m, 4 H); 1.41–1.32 (m, 12 H); 0.92
(t, 6 H, J ¼ 6.9 Hz). 13C NMR (300 MHz, CDCl3): d ¼ 166.4,
163.1, 152.8, 129.8, 129.6, 115.4, 115.3, 68.7, 68.6, 32.0, 29.3,
26.2, 22.8, 14.3; FT-IR (KBr disc, cmꢂ1): 2927, 2869, 2854, 1607,
1581, 1552, 1493, 1472, 1421, 1391, 1336, 1308, 1290, 1255, 1177,
1152, 1122, 1082, 1034, 1011, 951, 874, 816, 741, 728, 702, 656,
632; anal. calcd for C30H38N4O4: C, 69.47; H, 7.38; N, 10.80.
Found C, 69.57; H, 7.47; N, 10.77.
2,2-Bis(4-octyloxyphenyl)-bi-1,3,4-oxadiazole
1H NMR: (300 MHz, CDCl3), (ppm, from TMS): 8.15 (d, 4 H,
J ¼ 8.9 Hz); 7.05 (d, 4 H, J ¼ 8.9 Hz); 4.05 (t, 4 H, J ¼ 6.6 Hz);
1.86–1.79 (m, 4 H); 1.49–1.45 (m, 4 H); 1.35–1.30 (m, 16 H); 0.90
(t, 6 H, J ¼ 6.9 Hz); FT-IR (KBr disc, cmꢂ1): 2950, 2935, 2921,
2854, 1606, 1581, 1493, 1479, 1421, 1400, 1386, 1336, 1307, 1290,
1254, 1174, 1151, 1122, 1081, 1022, 1010, 998, 951, 845, 816, 741,
726, 702, 670, 656, 631; anal. calcd for C32H42N4O4: C, 70.30; H,
7.74; N, 10.25. Found C, 70.38; H,7.85; N, 10.17.
2,2-Bis(4-decyloxyphenyl)-bi-1,3,4-oxadiazole
1H NMR: (300 MHz, CDCl3), (ppm, from TMS): 8.16 (d, 4 H,
J ¼ 8.8 Hz); 7.05 (d, 4 H, J ¼ 8.8 Hz); 4.06 (t, 4 H, J ¼ 6.6 Hz);
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J. Mater. Chem., 2008, 18, 3954–3964 | 3963